Jonathan Daniels was a well-to-do kid from rural New Hampshire who enrolled in Virginia Military Institute in the late 1950s. After his father died abruptly in his sophomore year, Jonathan’s grief led to a reassessment of his priorities, and eventually he ended up in seminary. He was convicted by Martin Luther King Jr.’s call to come to Selma. There he witnessed the horrors his brothers and sisters were experiencing in Alabama. He would go back to Selma again and again—for a semester, for a summer—and in August 1965 he participated in a small protest and was jailed. After six days the group was released. While waiting for a ride home, they went into a grocery store to buy a drink. A deputy was threatening a black family, and Jonathan stepped in between them, pushing a young girl back out of the way. The deputy fired, and Jonathan was killed instantly.

Jonathan Daniels said a Yes that cost him his life. He embodied preacher William Sloane Coffin’s words about the kind of grace that allows us to risk “something big for something good.”

There’s an assumption that improv is a happy-go-lucky, no-holds-barred art form. But that glosses over the reality that Yes is risky. Saying Yes onstage is risky. Saying Yes in the midst of one’s life is even more so. And the risks don’t always work out the way we want. If they did, life would be a series of sure things rather than a string of chancy improvisations.

In a commencement speech for Knox College, Stephen Colbert talks about the risks that come from saying yes:

Now will saying “yes” get you in trouble at times? Will saying “yes” lead you to doing some foolish things? Yes it will. But don’t be afraid to be a fool. . . . People who pretend to be wise to the ways of the world are mostly just cynics. Cynicism masquerades as wisdom, but it is the farthest thing from it. Because cynics don’t learn anything. Because cynicism is a self-imposed blindness, a rejection of the world because we are afraid it will hurt us or disappoint us. Cynics always say no. But saying “yes” begins things. Saying “yes” is how things grow. Saying “yes” leads to knowledge. . . . So for as long as you have the strength to, say “yes.”

Yes is a hollow response if it doesn’t come with the possibility of everything going catastrophically wrong. Yes is infused with curiosity, mystery, and a hint of danger. We don’t know how life will turn out. It costs us something to step into that ambiguity.

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My friend Sarah says the riskiest Yes she ever said was submitting an application to adopt a child. She had planned for it for years, and had completed all the paperwork. But when it was all done except for pressing the “Send” button, her finger hovered in suspended animation for a long time. Was she really ready for this? The potential heartbreak of getting matched with a child, falling in love from afar, and having the adoption fall through? And on the other side, the messy, heart-expanding, freedom-killing, tear-filled, joy-infused task of loving a child forever?

Click. Yes.

Some of us step into these Yes moments more easily than others. I myself prefer that my backup plans have backup plans. Many of us need to start small, with some risky mini- Yeses to build a habit. Improv has been described as “creative cross-training,” because it gives us tools and habits that translate to the rest of our lives.

Many self-help books talk about creative risk in glowing terms. But sometimes our Yes crashes down, with hurtful impact. The gamble doesn’t pay off, and hearts get broken. It’s spiritually dishonest to suggest otherwise. As C. S. Lewis wrote, “Love anything and your heart will be wrung and possibly broken. If you want to make sure of keeping it intact you must give it to no one, not even an animal. Wrap it carefully ‘round with hobbies and little luxuries; avoid all entanglements. . . . To love is to be vulnerable.”